CN101543465A - Cosmetic composition comprising imidopercarboxylic acid derivative and n-acylated amino acid ester - Google Patents

Cosmetic composition comprising imidopercarboxylic acid derivative and n-acylated amino acid ester Download PDF

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CN101543465A
CN101543465A CN200910138734A CN200910138734A CN101543465A CN 101543465 A CN101543465 A CN 101543465A CN 200910138734 A CN200910138734 A CN 200910138734A CN 200910138734 A CN200910138734 A CN 200910138734A CN 101543465 A CN101543465 A CN 101543465A
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acid
group
dioxo
dihydro
alkyl
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R·普罗沃斯特
G·雷莫特
C·克莫范
C·莫赛
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LOreal SA
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
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Abstract

The invention relates to a cosmetic composition comprising an imidopercarboxylic acid derivative and an N-acylated amino acid ester, further to a cosmetic or a dermatological composition containing, in a physiologically acceptable medium, at least one imidopercarboxylic acid derivative and at least one N-acylated amino acid ester of formula (A), R'1(CO)N(R'2)CH(R'3)(CH2)n(CO)OR'4 (A), wherein n is equal to an integer of 0, 1 or 2, R'1 represents a straight-chain or branched-chain C5 to C21 alkyl or alkenyl, R'2 represents a hydrogen atom or a C1 to C3 alkyl group, R'3 represents a group selected from a hydrogen atom, methyl, ethyl, and straight-chain or branched-chain C3 or C4 alkyl chain, R'4 represents a straight-chain or branched-chain C1 to C10 alkyl group, or a straight-chain or branched-chain C2 to C10 alkenyl or sterol residue.

Description

Cosmetic composition containing iminopercarboxylic acid derivatives and N-acylamino acid esters
Technical Field
The invention relates to a composition, in particular a cosmetic or dermatological composition, comprising an iminopercarboxylic acid derivative and an N-acyl amino acid ester.
Background
It is known to use iminopercarboxylic acid derivatives in topical compositions, in particular in cosmetic or dermatological topical compositions, for example as bactericidal or antifungal agents. Their activity in anti-acne or whitening compositions is also known.
However, the use of these derivatives in this context entails the problem that these compounds are provided in crystalline form and that they are insoluble or only slightly soluble in water and in the lipid substances customary in the cosmetic or dermatological field. Thus, when used in topical compositions, they cannot be dissolved and are present in crystalline form, which can lead to irritation or discomfort to the skin upon use.
These derivatives can be partially soluble in lower alcohols, such as ethanol or isopropanol, or, for example, octyldodecanol, certain diols or short-chain fatty alcohols (below C)12) The solvent of (1). However, lower alcohols show the disadvantages of drying (drying out) and skin irritation; therefore, it is preferred to use in small amounts, in practice even zero, in body and/or face care products. Furthermore, these solubilizers can only be introduced in small amounts if the harmful changes in the cosmetic quality (mildness) and stability of the compositions comprising them are to be avoided.
Thus, there is a need to be able to dissolve iminopercarboxylic acid derivatives in physiologically acceptable media of cosmetic and/or dermatological compositions.
Disclosure of Invention
The Applicant company has found, surprisingly, that lipophilic amino acid derivatives in the form of esters are capable of solubilizing imidopercarboxylic acid derivatives without causing them to recrystallize.
The subject of the present invention is therefore a composition comprising, in a physiologically acceptable medium, at least one iminopercarboxylic acid derivative and at least one ester chosen from N-acyl amino acid esters of formula (A):
R′1(CO)N(R′2)CH(R′3)(CH2)n(CO)OR′4
(A)
wherein,
n is an integer equal to 0, 1 or 2,
R′1represents a straight or branched chain C5To C21An alkyl group or an alkenyl group, or a substituted or unsubstituted alkyl group,
R′2represents a hydrogen atom or C1To C3Alkyl radical，
R′3Represents a hydrogen atom, a methyl group, an ethyl group and a linear or branched C3Or C4The radical of an alkyl chain,
R′4represents a straight or branched chain C1To C10Alkyl or straight or branched C2To C10Alkenyl or sterol residues.
The term "physiologically acceptable medium" is understood to mean a medium compatible with keratinous substances, such as the skin, including the scalp, mucous membranes, eyes and hair.
The inventors of the present patent application have found that the use of lipophilic derivatives of amino acids in the form of esters unexpectedly enhances the solubility of the above-mentioned imidopercarboxylic acid derivatives and makes the resulting compositions stable for a long time (without crystal formation), stable also when the temperature is varied, and having satisfactory cosmetic properties.
Another subject of the invention comprises a cosmetic treatment process comprising the application of said composition to a keratinous substance.
Another subject of the invention is a process for dissolving imidopercarboxylic acid derivatives by means of the N-acylamino acid esters of formula (A) described above.
Iminopercarboxylic acid derivatives
The imidopercarboxylic acid derivatives used in the compositions according to the invention are preferably chosen from the compounds of formula (I) below:
Figure A200910138734D00071
wherein:
-R1and R2Each independently represents (i) a hydrogen atom; (ii) (C)1-C5) Alkyl, optionally selected from (C)1-C5) Alkoxy radicalRadicals, -OH groups, -COOH groups, -COOOH groups, -COOR4group-NO2One or more groups of radicals and halogen atoms are substituted, preferably one to three groups, wherein R is4Is defined as follows; or (iii) (C)1-C5) An alkoxy group,
-or, R1And R2Co-form
5-or 6-membered non-aromatic ring, wherein said 5-or 6-membered non-aromatic ring is optionally selected from (C)1-C5) Alkyl or (C)1-C5) One or more, preferably one to three, groups of alkoxy groups, wherein said (C) is substituted1-C5) Alkyl is optionally selected from (C)1-C5) Alkoxy, -OH group, -COOH group, -COOOH group, COOR4group-NO2One or more, preferably one to three, groups of radicals and halogen atoms;
-R and n are defined as follows:
or an aromatic ring A, to form more specifically an aromatic imidopercarboxylic acid derivative compound of formula (II),
Figure A200910138734D00081
wherein:
-A represents a benzene or naphthalene ring, optionally substituted by R3、(C1-C5) Alkoxy, -OH group, -COOH group, -COOOH group, -COOR4group-NO2One or more, preferably up to 4, more preferably 1 or 2, groups of radicals and halogen atoms are substituted,
-R is a group or groups, which are identical or different, which represent a hydrogen atom, -OH group, -COOH group, -COOOH group, -COOR group4Group or R3The radical(s) is (are),
oR3is represented by (C)1-C5) Alkyl, optionally selected from (C)1-C5) Alkoxy, -OH group, -COOH group, -COOOH group, -COCR4group-NO2One or more, preferably one to three, of the radicals and halogen atoms are substituted,
oR4is represented by (C)1-C5) An alkyl group, optionally selected from (C)1-C5) Alkoxy, -OH group, -COOH group, -COOOH group, -COOR5Radical substitution of radicals in which R5Is (C)1-C5) Alkyl, and
n is an integer varying between 1 and 5, such as 1 to 3, or such as 3 to 5.
It is understood that the compounds of formula (I) or (II) comprise all possible enantiomers and mixtures thereof and also the corresponding salts or any dimers of the compounds of formula (I) or (II).
Among these salts, mention may be made, for example, of potassium or ammonium salts.
(C1-C5) Examples of alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and pentyl. (C)1-C5) Among the alkoxy groups that may be mentioned are methoxy or ethoxy groups. Among the halogen atoms that may be mentioned are fluorine, chlorine and bromine.
In the substituted (C)1-C5) Among the alkyl radicals which may be mentioned in particular are the radicals-CH2OCH3、-CH2OC2H5、-CH2OH、-CH2COOH、-CH2COOOH、-CH2CH2COOH、-CH2CH2COOOH、-CH2Cl、-CH2F、-CF3and-CH2COOC2H5A group.
According to one embodiment, the R group is a hydrogen atom.
According to another embodiment, a represents a phenyl ring.
According to another embodiment, A is substituted with at least one-COOH group or one-COOOH group.
Finally, according to another embodiment, a is unsubstituted.
According to one embodiment, aromatic imidopercarboxylic acid derivatives of formula (II) are used in which A is an unsubstituted benzene or naphthalene ring, R is a hydrogen atom, a-COOOH group or (C)1-C3) Alkyl, optionally substituted with-COOOH groups or-COOH groups, and n varies between 3 and 5.
Among the compounds of formula (I), the following may be mentioned: 2, 5-dihydro-3-methyl-2, 5-dioxo-1H-pyrrole-1-peroxyhexanoic acid (R)1＝H，R2Me; n ═ 5), 2, 5-dihydro-2, 5-dioxo-1H-pyrrole-1-peroxyhexanoic acid (R)1＝R2H; n-5) and 1, 3, 4, 5, 6, 7-hexahydro-1, 3-dioxo-2H-isoindole-2-peroxobutanoic acid (R)1And R2A 6-membered ring; n-3).
Among the compounds of formula (II), the following general names may be mentioned: phthalimidoperacetic acid (a ═ benzene; n ═ 1), 3-phthalimidoperpropionic acid (a ═ benzene; n ═ 2), 2-phthalimidodiperoxosuccinic acid (a ═ benzene; R ═ COOOH; n ═ 2), 3-phthalimidoperbutanoic acid (a ═ benzene; R ═ CH ═3(ii) a n ═ 2), 2-phthalimidoperpropionic acid (a ═ benzene; r is CH3(ii) a n ═ 1), the methyl half ester of 2-phthalimido monoperpentanedioic acid (a ═ benzene; r is-COOOMe; n ═ 3), 3-phthalimido diperoxyadipic acid (a ═ benzene; r is COOOH; n ═ 4), naphthalimido peroxyacetic acid (a ═ naphthalene; n ═ 1), 2-phthalimido monopersuccinic acid (a ═ benzene; r is COOH; n-2) and 4- (4-percarboxy phthalimido) perbutyric acid.
Among the compounds of formula (II), there may also be mentioned the following compounds referred to by CAS nomenclature:
compounds in which a is a benzene ring, for example 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-butane-peroxyacid (peroxoic acid), also known as benzenedicarboxyiperoxobutyric acid, 3-benzenedicarboxyiminoperoxybutyric acid or 4-benzenedicarboxyiminoperoxybutyric acid (n ═ 3), 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxyvaleric acid (n ═ 4), 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxyhexanoic acid (n ═ 6), 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxyoctanoic acid (n ═ 7) or benzenedicarboxyiminoperoxyoctanoic acid, 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxynonanoic acid (n ═ 8), 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxydecanoic acid (n ═ 9), 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxyundecanoic acid (n ═ 10) or 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxydodecanoic acid (n ═ 11);
compounds in which a is a substituted benzene ring, for example 1, 3-dihydro-5- (hydroperoxycarbonyl) -1, 3-dioxo-2H-isoindole-2-peroxybutyric acid (n ═ 3, substituted with a-COOOH group) or 1, 3-dihydro-4- (hydroperoxycarbonyl) -1, 3-dioxo-2H-isoindole-2-peroxybutyric acid (n ═ 3, substituted with a-COOOH group);
-a is a benzene ring and at least one R group is different from a hydrogen atom, such as 3- (1, 3-dihydro-1, 3-dioxo-2H-isoindol-2-yl) bisperoxyhexanoic acid (n ═ 3, R ═ CH)2COOOH), (1, 3-dihydro-1, 3-dioxo-2H-isoindol-2-yl) diperoxybutyric acid (R ═ COOOH, n ═ 2), 2- (1, 3-dihydro-1, 3-dioxo-2H-isoindol-2-yl) diperoxypentanoic acid (R ═ COOOH, n ═ 3), the 5-methyl ester of 4-phthalimido monoperoxyglutaric acid (R ═ COOMe, n ═ 3) or 1, 3-dihydro- β -methyl-1, 3-dioxo-2H-isoindol-2-peroxopropionic acid, also known as β -methyl-1, 3-dioxo-2-isoindoline peroxopropionic acid or 3-phthalimido-perbutyric acid (R ═ Me, n-2).
The following salts may also be mentioned: n- (2-hydroxyethyl) -N, N-dimethyl-1-dodecylammonium salt of 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxyhexanoic acid (1: 1).
According to another form, the compound of formula (II) is phthalimido peroxycaproic acid, also known as 6- (phthalimido) peroxycaproic acid, epsilon- (phthalimido) peroxycaproic acid or PAP. It has the following chemical structure:
which corresponds to a compound of formula (II) wherein the R group represents a hydrogen atom, a represents an unsubstituted benzene ring and n ═ 5.
Finally, among the acceptable dimers of the compounds of formula (II) that may be mentioned are the dimers of PAP, also known as 5, 7-dihydro-1, 3, 5, 7-tetraoxobenzo- [1, 2-c: 4, 5-c ] dipyrrole-2, 6(1H, 3H) -diperoxyahexanoic acid, of the formula:
Figure A200910138734D00111
by way of example, the content of active starting materials, i.e. iminoperoxyacid derivatives, in particular compounds of formula (I) or (II), which can be used in the present invention, can range, for example, from 0.01 to 5% by weight, in particular from 0.01% to 2% by weight, preferably from 0.15 to 1.5% by weight and more preferably from 0.3% to 1% by weight, based on the total weight of the composition.
Phthalimidoperoxycaproic Acid (PAP) or Phthalimidoperoxycaproic Acid (PAP) is available, particularly in two commercial forms from Solvay.
Thus, phthalimidoperoxycaproic acid may be used in combination with cyclodextrins to improve the stability of the compounds.
The document EP 895777 is mentioned in its introduction and describes in particular the adduct of epsilon-phthalimidoperoxycaproic acid with cyclodextrin.
This encapsulated product is sold under the trade name Eureco by Solvay
Figure A200910138734D0011151439QIETU
HC-P11 (a powdered inclusion complex of phthalimidoperoxycaproate with pharmaceutical grade beta-cyclodextrin) is sold.
Phthalimidoperoxycaproic acid is also known under the trade name Eureco
Figure A200910138734D0011151439QIETU
HCL17 was provided in the form of an aqueous dispersion (including 17% active). Phthalimidoperoxycaproic acid is also known under the trade name Eureco
Figure A200910138734D0011151439QIETU
HC-P11 is provided in powder form. Such phthalimidoperoxycaproic acid in the form of an aqueous dispersion is described in document EP 1074607. These aqueous dispersions are prepared by reacting methyl vinyl ether with maleic acid and/or anhydride in a ratio of 1: 1 and the copolymer of the alternating structure is stabilized.
Alternative formulations comprising imidopercarboxylic acid derivatives may also be used to implement the present invention. Likewise, particular mention may be made of dispersions, in particular aqueous dispersions, as described, for example, in patent application WO2004/110610, capsules comprising a gel matrix as described, for example, in patent application WO2004/110611, capsules based on inorganic salts as described, for example, in application WO2004/110612 or multi-layer capsules comprising at least one polyelectrolyte and/or one ionic surfactant as described, for example, in application WO 2004/110613.
N-acyl amino acid esters
The esters in the composition according to the invention are advantageously chosen from N-acyl amino acid esters of formula:
R′1(CO)N(R′2)CH(R′3)(CH2)n(CO)OR′4
n is an integer equal to 0, 1 or 2,
R′1represents a straight or branched chain C5To C21An alkyl group or an alkenyl group, or a substituted or unsubstituted alkyl group,
R′2represents a hydrogen atom or C1To C3An alkyl group, a carboxyl group,
R′3represents a hydrogen atom, a methyl group, an ethyl group and a linear or branched C3Or C4The radical of an alkyl chain,
R′4represents a straight or branched chain C1To C10Alkyl or straight or branched C2To C10Alkenyl or sterol residues.
In the formula of the amino acid ester represented by the above formula, R'1The (CO) -group is the acyl radical of an acid, preferably selected from the group consisting of capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linoleic acid, linolenic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, coconut oil fatty acid and palm oil fatty acid. In addition, these fatty acids may also possess hydroxyl groups. More preferably, the fatty acid is lauric acid.
N (R ') of amino acid ester'2)CH(R′3)(CH2)nThe (CO) -moiety is preferably selected from the following amino acids: glycine, alanine, valine, leucine, isoleucine, serine, threonine, proline, hydroxyproline, β -alanine, aminobutyric acid, aminocaproic acid, sarcosine or N-methyl- β -alanine.
More preferably, the amino acid is sarcosine.
Corresponding OR4The amino acid ester portion of the group may be selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, t-butanol, isobutanol, 3-methyl-1-butanol, 2-methyl-1-butanol, fusel oil, pentanol, hexanol, cyclohexanol, octanol, 2-ethylhexanol, decanol, dodecanol, tetradecanol, hexadecanol, the reaction product of hexadecanol and the glycol ether of hexadecanol polyethylene (cetearyl alcohol),Stearyl alcohol, oleyl alcohol, behenyl alcohol, jojoba alcohol, 2-cetyl alcohol, 2-octyldodecanol, and isostearyl alcohol.
These amino acid esters can be obtained in particular from natural sources of amino acids. In this case, the amino acids are obtained from the hydrolysis of natural vegetable proteins (oat, wheat, soybean, palm or coconut) and then it is necessary to obtain a mixture of amino acids which must then be esterified and then N-acylated. The preparation of such amino acids is more particularly described in patent application FR 2796550, which is incorporated herein by reference.
An N-acyl amino acid ester more particularly preferred for use in the present invention is isopropyl N-lauroyl sarcosinate, of the formula:
Figure A200910138734D00131
this product is sold by Ajinomoto under the name Eldew SL-205 below.
The content of the N-acyl amino acid ester as described above in the composition of the invention ranges from 0.05 to 50% by weight, preferably from 1 to 30% by weight and more preferably from 1 to 10% by weight, relative to the total weight of the composition.
According to a preferred embodiment, the content of active substance N-acyl amino acid ester and iminopercarboxylic acid derivative of formula (I) in the composition according to the invention is such that the ratio of N-acyl amino acid ester to iminopercarboxylic acid derivative ranges from 5 to 25, and better still from 10 to 20.
The composition may also include a fatty phase which may include oils, gums or waxes commonly used in the contemplated application areas. When oils or waxes are used in the present invention, mineral oils (liquid paraffin), vegetable oils (liquid fractions of shea butter, sunflower oil, almond oil, rice bran oil, etc.), animal oils (perhydrosqualene), synthetic oils (bird feather oil (Purcellin oil)), silicone oils or waxes (cyclomethicone, dimethicone), and fluorinated oils (perfluoropolyethers), beeswax, carnauba wax, paraffin, shea butter, or hydrogenated jojoba oil may be mentioned. Fatty alcohols (cetyl, stearyl, etc.) and fatty acids (stearic acid, etc.) may also be added to these oils.
When the composition is an emulsion, the proportion of fatty phase is from 5% to 80% by weight, preferably from 5% to 50% by weight, relative to the total weight of the composition. The oils, waxes, emulsifiers and co-emulsifiers used in the emulsion composition are selected from those commonly used in the cosmetic field. The emulsifiers and co-emulsifiers are present in the composition in a proportion of 03 to 30% by weight and preferably 0.5 to 20% by weight, relative to the total weight of the composition. Lipid vesicles (lipid vesicles) may additionally be included in the emulsion.
When the composition is an oily solution or gel, the fatty phase constitutes more than 90% of the total weight of the composition.
The compositions may also comprise adjuvants commonly used in the art, such as surfactants, emulsifiers, hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic additives, preservatives, antioxidants, solvents, fragrances, fillers, masking agents, odor absorbers, coloring substances or other cosmetic or dermatological active substances. These various additives are conventionally used in the cosmetic field, for example, in an amount of 0.01 to 10% by weight based on the total weight of the composition. These additives are introduced into the fat phase, the aqueous phase and/or the lipid globules, respectively, depending on their nature.
Surfactants which can be used are, for example, glyceryl stearate, polysorbate 60, the name Tefose by the company Gattefose
Figure A200910138734D0011151439QIETU
PEG-6/PEG-32/glycol stearate mixture, PEG stearate derivatives or sugar derivatives sold as 63.
Mention may be made, as hydrophilic gelling agents which can be used in the present invention, of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylic acid/alkyl acrylate copolymers, polyacrylamides, polysaccharides such as hydroxypropylcellulose, natural gums and clays; and lipophilic gelling agents which may be mentioned are modified clays, such as, for example, bentones, metal salts of fatty acids, such as, for example, aluminum stearate, hydrophobic silica, ethylcellulose or polyethylene.
The composition may be provided in any form that is contemplated.
In particular, the composition may have the form: aqueous, alcoholic, aqueous/alcoholic or oily solutions; dispersions of the lotion (position) or serum (serum) type; water-in-oil, oil-in-water, or multiple emulsions; a suspension; microcapsules or microparticles; vesicular dispersions of ionic and/or non-ionic type; lotions in the form of an aqueous or oily lotion or slurry; foaming; solid formulations, such as stick formulations; an aerosol composition further comprising a compressed propellant; or in the form of a patch.
The compositions which may be used in the present invention may be provided in the form of hair care compositions, in particular: shampoos, hair-setting lotions, care lotions (styling lotions), setting creams or setting gels (styling gels), coloring compositions (dyeing compositions), in particular oxidative coloring compositions, hair-restyling lotions (hair restyling compositions), permanent wave compositions (permanent compositions), in particular compositions for the first step of permanent waving (permanent wave), lotions or gels for combating hair loss or anti-parasitic shampoos. It may also be provided to the face, hands, feet, major anatomical folds or the body (e.g. day cream, night cream, makeup remover cream, sunscreen composition, body protection or care cream, after sun cream, lotion, skin lotion for skin care, gel or foam, e.g. cleansing lotion, artificial coloring composition) in the form of a cleansing, protecting, treating or caring composition; body or face make-up compositions such as foundations; a bath composition; deodorant compositions include, for example, antibacterial agents; an after-shave composition (after-shave composition); an epilatory composition; compositions against insect stings or bites; a pain-relieving composition; or compositions for treating certain skin disorders, such as eczema, rosacea, psoriasis or severe pruritus. When the composition according to the invention is used in exfoliating products, it can also be provided in the form of the above-mentioned human and preparation, provided that it is easily removed by washing, in particular as a hydrogel or an aqueous or aqueous/alcoholic solution. Application can also be carried out in any manner in which it is possible to achieve uniform distribution, in particular using a cotton swab (swab), a stick, a brush, a gauze, a scraper (spatula) or a pad or also by spraying, and washing off by water or using mild detergents. By a preferred embodiment of the present invention, it is proposed that the composition for chemical peeling will comprise a continuous aqueous phase.
It can be provided in all forms normally used for topical application, in particular in the form of aqueous/alcoholic solutions, oil-in-water or water-in-oil or multiple emulsions, oil-containing gels or anhydrous products in liquid, paste-like or solid form or in the form of dispersed pellets; these beads may be polymeric nanoparticles, such as nano-beads or nano-capsules, or lipid vesicles of ionic or non-ionic type. These compositions are prepared according to the usual methods.
The composition may be more or less fluid and have a white or coloured cream appearance, an ointment, cream, lotion, slurry, patch or foam. It may optionally be applied to the skin or hair in the form of an aerosol. It may also be provided in solid form, for example in rod form.
Detailed Description
The following examples are intended to illustrate the invention without limiting it.
Example 1: aqueous gel
By weight%
Sodium hydroxide 0.37
Citric acid 0.37
Phthalimido peroxycaproic acid, from Solvay
Figure A200910138734D0015151719QIETU
HCL17(17
Active substance) 5% by weight
Cetyl alcohol 1
N-lauroylsarcosine isopropyl ester (Eldev SL-205 from Ajinomoto) 10
Glyceryl stearate/polyethylene glycol (100EO) stearate mixture (from Croda)
Arlacel165FL) 0.6
Cross-linked acrylate/acrylic acid C10-C30Polymers of alkyl esters (from Noveon)
Carbopol Ultrez-20) 0.9
Polyethylene glycol (8EO) 6
0.2% of preservative
The balance of water is 100
Step (ii) of
The Carbopol was sprayed into the aqueous phase at room temperature (25 ℃) and allowed to stand for 10 minutes, allowing the powder to soak in water. The mixture was stirred with a Rayneri mixer and then sodium hydroxide was added with increasing stirring. After obtaining a gel without clumping, preservatives, citric acid and PEG-8 were added, followed by PAP (which had been stirred with a stick for a few minutes in advance). Stirring was maintained at high speed for several minutes. Meanwhile, a fat phase was prepared by heating cetyl alcohol, N-lauroyl sarcosinate and Arlacel to 50 deg.C, and then, the fat phase was emulsified in the hydrogel prepared as above and vigorously stirred for 10 minutes.
Comparative examples 2 to 7
The following compositions were prepared
Comparison of invention comparison of comparison
Example 2 example 3 example 4 example 5 example 6 example 7
Wt%
Phase A
Sodium hydroxide 0.20.20.20.20.20.2
EDTA disodium 0.050.050.050.050.050.05
Trisodium citrate 0.050.050.050.050.050.05
Zinc gluconate 0.10.10.10.10.10.1
Citric acid 0.30.30.30.30.30.3
Salicylic acid 0.60.60.60.60.60.6
Eucalyptus leaf extract 0.020.020.020.020.020.02
Xanthan gum 0.20.20.20.20.20.2
Glycerol 555555
Antiseptic 111111
Water to balance
100 100 100 100 100 100
Phase B
2-Octyldodecanol 111111
5- (n-octanoyl) salicylic acid
0.1 0.1 0.1 0.1 0.1 0.1
Acid(s)
A polydimethylsiloxane (poly (dimethylsiloxane) and a polydimethylsiloxane (polydimethylsiloxane),
100cSt (from Dow)
0.5 0.5 0.5 0.5 0.5 0.5
Comming's DC200
Fluid)
Cyclohexane dimethyl silicon
Siloxane
(cyclohexadimethy
8.5 8.5 8.5 8.5 8.5 8.5
lsiloxane), 8cSt (from
From Dow Corning
DC246Fluid)
Cetyl alcohol 0.250.250.250.250.250.25
N-lauroylsarcosine
Isopropyl ester (from)
7.5
Of Ajinomoto
Eldew SL-205)
Propylene carbonate 7.5
Hexyldecanol 7.5
Octyl-2-dodecanol 7
Branched C12-C13 alcohols
Of benzoic acid esters (from)
7 of Sasol
COSMACOL
ELI)
Polyethylene glycol
7.5
400(8OE)
Glyceryl stearate/poly
Ethylene glycol (100EO) hard
Mixture of fatty acid esters (Lai 111111)
Arlacel from Croda
165FL)
Phase C
Partially neutralized by ammonia
Crosslinked polyacryl 222222
Aminomethylpropane sulfonic acid
(from Clariant)
Hostacerin AMPS)
Phase D
Phenylimidoyl
Peroxy caproic acid from
Of Solvay
Figure A200910138734D0018152512QIETU
2.5 2.5 2.5 2.5 2.5 2.5
HCL17 (17% by weight)
Active substance of (2)
Phase E
Ethanol 555555
Phase F
A polyamide fiber,
0.9dtex, length 333333
0.3(Utexbel)
Step (ii) of
Phase a and part of the water were heated to 80 ℃ with stirring in a Rayneri mixer and the mixture was cooled to 65 ℃. Phase B, previously heated in a water bath, is added to phase A (emulsified phase) with stirring in a mixer. The mixture was cooled to 45 ℃, the remaining water was added to dilute, and C, D, E and phase F were added sequentially with stirring. Phase D may also be added in the dilution step prior to addition of phase C.
Evaluation of the appearance of the composition:
comparative examples
2 3 4 5 6
Appearance of the product
Presence of crystals, very coarse and very coarse
The emulsion is uniform, and the emulsion is uniform,
the emulsion visible in the macroemulsion, the emulsion,
no crystal
The existence of crystallization in the presence of oil-containing globules
Only the N-acyl amino acid esters of the present invention provide good dissolution of phthalimidoperoxycaproic acid and provide a homogeneous, non-crystalline emulsion relative to other solvents.

Claims (13)

1. Cosmetic or dermatological composition comprising, in a physiologically acceptable medium, at least one iminopercarboxylic acid derivative and at least one ester chosen from N-acyl amino acid esters of formula (A):
R′1(CO)N(R′2)CH(R′3)(CH2)n(CO)OR′4
(A)
wherein:
n is an integer equal to 0, 1 or 2,
R′1denotes a straight or branched chainC of (A)5To C21An alkyl group or an alkenyl group, or a substituted or unsubstituted alkyl group,
R′2represents a hydrogen atom or C1To C3An alkyl group, a carboxyl group,
R′3represents a hydrogen atom, a methyl group, an ethyl group and a linear or branched C3Or C4The radical of an alkyl chain,
R′4represents a straight or branched chain C1To C10Alkyl or straight or branched C2To C10Alkenyl or sterol residues.
2. The composition of claim 1 wherein the imidopercarboxylic acid derivative is a derivative of formula (I):
Figure A200910138734C00021
wherein:
-R1and R2Each independently represents (i) a hydrogen atom; (ii) (C)1-C5) Alkyl, optionally selected from (C)1-C5) Alkoxy, -OH group, -COOH group, -COOOH group, -COOR4group-NO2One or more, preferably one to three, groups of radicals and halogen atoms are substituted, where R is4Is defined as follows; or (iii) (C)1-C5) An alkoxy group,
-or, R1 and R2 together form
5-or 6-membered non-aromatic ring, wherein the 5-or 6-membered non-aromatic ring is optionally selected from (C)1-C5) Alkyl radical or (C)1-C5) One or more, preferably one to three, of the alkoxy groups, wherein (C) is1-C5) The alkyl group is optionally selected from (C)1-C5) Alkoxy, -OH group, -COOH group, -COOOH group, -COOR4group-NO2One or more, preferably one to three, groups of radicals and halogen atoms; and
-R and n are defined as follows:
or an aromatic ring A, to form more specifically an aromatic imidopercarboxylic acid derivative compound of formula (II),
Figure A200910138734C00031
wherein:
-A represents a benzene or naphthalene ring, optionally substituted by R3、(C1-C5) Alkoxy, -OH group, -COOH group, -COOOH group, -COOR4group-NO2One or more, preferably up to 4, more preferably 1 or 2, groups of radicals and halogen atoms are substituted,
-R is a group or groups, which are identical or different, which represent a hydrogen atom, -OH group, -COOH group, -COOOH group, -COOR group4Group or R3The radical(s) is (are),
ο R3is represented by (C)1-C5) Alkyl, optionally selected from (C)1-C5) Alkoxy, -OH group, -COOH group, -COOOH group, -COOR4group-NO2One or more, preferably one to three, of the radicals and halogen atoms are selected from the group consisting of radical substitution,
ο R4is represented by (C)1-C5) An alkyl group, optionally selected from (C)1-C5) Alkoxy, -OH group, -COOH group, -COOOH group, -COOR5Radical substitution of radicals in which R5Is (C)1-C5) An alkyl group, and
n is an integer varying between 1 and 5, such as 1 to 3, or such as 3 to 5.
3. The composition of claim 2, wherein R is a hydrogen atom.
4. A composition according to claim 2 or 3, wherein a is a benzene ring.
5. The composition according to any one of claims 1 to 4, wherein the compound of formula (I) is selected from the group consisting of 2, 5-dihydro-3-methyl-2, 5-dioxo-1H-pyrrole-1-peroxyhexanoic acid, 2, 5-dihydro-2, 5-dioxo-1H-pyrrole-1-peroxyhexanoic acid and 1, 3, 4, 5, 6, 7-hexahydro-1, 3-dioxo-2H-isoindole-2-peroxybutyric acid.
6. A composition according to any one of the preceding claims, wherein the imidopercarboxylic acid derivative is selected from the group consisting of phthalimidoperacetic acid, 3-phthalimidoperpropionic acid, 2-phthalimidoperosuccinic acid, 3-phthalimidoperbutanoic acid, 2-phthalimidoperpropanoic acid, the methyl half-ester of 2-phthalimidoperpentaric acid, 3-phthalimidodiperoxyadipic acid, naphthaliminoperoxyacetic acid, 2-phthalimidoperosuccinic acid, 4- (4-percarboxyphthalimido) perbutanoic acid, 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxobutanoic acid, 3-phthalimidoperbutanoic acid, 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxypentanoic acid, 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxyhexanoic acid, 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxyoctanoic acid, 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxynonanoic acid, 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxydecanoic acid, 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxyundecanoic acid, and mixtures thereof, 1, 3-dihydro-1, 3-dioxo-2H-isoindol-2-peroxydodecanoic acid, 1, 3-dihydro-5- (hydroperoxycarbonyl) -1, 3-dioxo-2H-isoindole-2-peroxybutyric acid, 1, 3-dihydro-4- (hydroperoxycarbonyl) -1, 3-dioxo-2H-isoindole-2-peroxybutyric acid, 3- (1, 3-dihydro-1, 3-dioxo-2H-isoindol-2-yl) bisperoxyhexanoic acid, (1, 3-dihydro-1, 3-dioxo-2H-isoindol-2-yl) bisperoxybutyric acid, alpha-hydroxy-methyl-ethyl-propyl-2-methyl-propyl-2-hydroxy-ethyl-propyl-2H-isoindol, 2- (1, 3-dihydro-1, 3-dioxo-2H-isoindol-2-yl) diperoxypentanoic acid, 5-methyl ester of 4-phthalimido monoperoxyglutaric acid, 1, 3-dihydro- β -methyl-1, 3-dioxo-2H-isoindole-2-peroxopropionic acid and the N- (2-hydroxyethyl) -N, N-dimethyl-1-dodecylammonium salt of 1, 3-dihydro-1, 3-dioxo-2H-isoindole-2-peroxohexanoic acid (1: 1).
7. A composition according to any preceding claim, wherein the imidopercarboxylic acid derivative is phthalimidoperoxycaproic acid.
8. A composition according to any one of the preceding claims, wherein the iminopercarboxylic acid derivative is present as active substance in a quantity ranging from 0.01% to 5% by weight, in particular from 0.01% to 2% by weight, preferably from 0.15% to 1.5% by weight and more preferably from 0.3% to 1% by weight, relative to the total weight of the composition.
9. A composition according to any preceding claim, wherein the N-acyl amino acid ester is isopropyl N-lauroylsarcosine.
10. Composition according to any one of the preceding claims, characterized in that the content of said N-acyl amino acid ester is from 0.05 to 50% by weight, preferably from 1 to 30% by weight, more preferably from 1 to 10% by weight, relative to the total weight of the composition.
11. Composition according to any one of the preceding claims, characterized in that the content of N-acyl amino acid ester and iminopercarboxylic acid derivative of formula (I) as active substances in the composition according to the invention is such that the ratio of N-acyl amino acid ester to iminopercarboxylic acid derivative is in the range 5 to 25.
12. Cosmetic treatment process comprising the application to a keratinous substance of a composition according to any one of claims 1 to 11.
13. A method for dissolving an imidopercarboxylic acid derivative by an N-acylamino acid ester of formula (A):
R′1(CO)N(R′2)CH(R′3)(CH2)n(CO)OR′4
(A)
wherein:
n is an integer equal to 0, 1 or 2,
R′1represents a straight or branched chain C5To C21An alkyl group or an alkenyl group, or a substituted or unsubstituted alkyl group,
R′2represents a hydrogen atom or C1To C3An alkyl group, a carboxyl group,
R′3represents a hydrogen atom, a methyl group, an ethyl group and a linear or branched C3Or C4The radical of an alkyl chain,
R′4represents a straight or branched chain C1To C10Alkyl or straight or branched C2To C10Alkenyl or sterol residues.
CN200910138734A 2008-03-28 2009-03-27 Cosmetic composition comprising imidopercarboxylic acid derivative and n-acylated amino acid ester Pending CN101543465A (en)

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